Vesting Schedules – Beyond the Standard

TL;DR: The standard 4-year with a 1-year cliff vesting schedule is not the only option. Companies can use a number of alternatives to better align incentives, and even select for employees/founders with more loyalty and interest in long-term commitment.

This is not a post explaining what vesting schedules are – I make it a point to (try to) not duplicate content that others have already written about 10x on the web. See this post for a quick run-down.

Most people know that the “market standard” vesting schedule is 4-years with a 1-year cliff. That’s standard for employees, but also quite common for founders. I occasionally hear founders say that a founder team shouldn’t subject each other to a cliff, but generally I think that’s a bad idea. Some kind of cliff is a great way of ensuring that anyone there on Day 1 intends to be there for some meaningful amount of time. If they balk at a cliff, it says something; not entirely clear what it says, but it certainly says something of significance.

Advisors tend to have shorter schedules, like 1-2 years, because their grants are smaller and tenure tends to also be shorter. At least a 3-month cliff is always a good idea for advisors, in my opinion. If they balk, it, again, says something.  Making small, reasonable requests in any kind of relationship, and observing the response carefully, can be a great way to gauge a person’s personality, motivations, and perspective; even if you consider the request itself immaterial and easy to drop. 

However, for companies that feel like the standard approach doesn’t fit their context, or align incentives properly, there are a lot of smart alternatives that we’ve seen our client base adopt. Here are a few:

Milestone Vesting

Instead of vesting based on time, you set it to occur upon certain milestones. These can be any number of things: achieving a certain financing, a certain revenue level, hitting a sales quota, etc. Whenever we see milestone vesting, the milestones tend to be contextualized for the individual. And certainly it only makes sense to have milestones that the individual recipient of the stock actually plays a lead role in achieving.

The benefit of milestone vesting is it can, when it works, better align “earning” equity with actually delivering results, as opposed to simple tenure based on time. However, the challenges that arise are (i) in the drafting – getting people to agree on reasonable milestones, (ii) in deciding when they’ve been achieved – who ultimately decides? the Board? the CEO?, and (iii) when circumstances change and ambiguity arises as to whether the milestone has been met. And of course, it is just more of a hassle to have to track milestones for vesting purposes as opposed to just letting the clock tick.

My strong suggestion to clients whenever they go with milestone vesting is to stick to milestones with objective, unambiguous metrics. Stay away from anything that depends on someone’s opinion – like “doing X to the satisfaction of Y person.” You’re just asking for trouble if you go there. Something like “achieving $X in cumulative customer revenue” will result in far far fewer disputes. And remember to use milestones that the stock recipient plays a significant role in helping the Company achieve. That too will prevent arguments over unfairness or bad faith as to person Y being responsible for why person X didn’t get their vested equity.

Longer Schedules (5-6 years)

There is a lot of value in attracting employees who intend to be with your company for the long-haul, as opposed to those who hop between employers. The sense of long-term thinking and loyalty that a long-term employee can bring to key projects can be hugely important strategically. I’ve always found the “perk wars” of certain tech ecosystems to be somewhat counter-productive, as they tend (in my mind) to select for employees with more mercenary personalities, as opposed to people who want to be there for much more important reasons.

I’ve certainly applied that thinking to how I recruit for MEMN.  Honestly, if whether or not we offer free lunch or doggy sitting will influence your decision to work for us, I’d prefer you not.

Companies that deeply value long-term commitment will often consider having longer-than-standard vesting schedules; maybe 5 or 6 years. Of course, for this to work you generally need to provide an appropriately larger equity stake.  Someone might ask why not, instead of one grant with a longer schedule, simply committing to do another grant after the standard 4-years?

It’s true that you can do that, and the standard approach is to provide ‘fresh’ grants to employees, for retention purposes, once their original vesting schedules run their course. However, (i) a grant made years later will have a higher exercise/purchase price (for tax purposes), so it’s actually tax favorable to do an earlier grant with a larger schedule, and (ii) there’s something about a longer schedule that just signals a person’s long-term commitment better, particularly if coupled with back-weighted vesting (see below).

Back-Weighted Schedules

If you’re looking to use vesting schedules as a way to gauge long-term commitment, back-weighted vesting is definitely an option worth considering. The concept is quite simple. Instead of vesting in equal installments over a schedule, the back-end of the schedule provides more vesting than the front-end. So instead of 25% vesting per year, Year 1 may be only 10%, but Year 4 may be 40%. There is definitely some logic to this idea, because the value someone delivers to their employer tends to go up over time, as they’ve become integrated into the culture, moved up in rank, taken on more responsibility, etc.

A longer-than-standard schedule with back-weighted vesting is one of the strongest messages you can send as to how much significance the Company places on loyalty and long-term employment. And as I mentioned before, if someone really balks at the idea, pay attention to what that tells you, because it definitely tells you something.

For key hires, the standard doesn’t always fit. 

I hear it all the time: “just go with what’s standard.” I understand that approach, and it’s sometimes driven by an attitude that all of this legal mumbo jumbo doesn’t matter. Except for when it does.

For strategic hires, particularly in the very early days of a Company when your core team will totally make or break you, non-standard vesting schedules can be a valuable tool to align incentives, and “filter” for people who may not be as committed to the cause as you think they are. Remember: when someone says “no” to something you think is reasonable, it may not be fully clear why, but it tells you something. And that something can be very important. 

Fatal Errors in Early Startup Hiring

I don’t pretend to be an expert in HR or tech recruiting, at all. However, being a VC lawyer gives you a deep inside view into a lot of what goes right and what goes wrong in early-stage hiring for startups; particularly what goes wrong, because that’s usually when lawyers get called in. Lots of data points to notice patterns. While there are a whole lot more issues that I’m not covering, below are a few key recruiting errors (tactical, not legal) that I’ve regularly seen Founder CEOs make as they start trying to expand their roster.

Hiring Sociopaths

Well that escalated quickly, didn’t it. Very very very^2 few people are so talented that they can make up for having a toxic personality. What is toxic? Someone who either (i) can’t control their own emotions, or (ii) seems to somehow regularly trigger other peoples’ emotions, in a bad way.

The early days of a startup are chaotic. You need personalities that will absorb some of that chaos, and make it easier to manage, not harder. Character and values are at least as important as the person’s skillset. When I hire lawyers, I pay at least as much attention to subtle cues in a person’s behavior as I do to their analytical skills; their facial expressions, manner of speaking, how they react to others, how they describe other people and themselves. I’ve seen what it’s like to work in places where there is even just 1 super toxic personality. It ruins everything, and can sink a company.

That doesn’t mean emotions in general are bad. Emotion often means you care about something. It’s OK for people to get emotional about stuff; better than people who are disengaged and stoic all the time. But there’s a world of difference between getting emotional because you care about something v. just because you can’t control yourself, or don’t want to. Blind reference checks help a lot.

Hiring “Big Company” People

Jeff Bussgang’s “jungle, then dirt road, then highway” metaphor is valuable for understanding how you can go wrong in hiring people who aren’t the right fit for a startup environment. A Series C or later company operates extremely differently from how a seed or Series A company does. Later-stage companies have higher salaries, more narrowly defined roles, more predictability, more formality, more perks. Earlier stage means lower salaries (but more equity), more flexible and broad roles designed to ‘just get it done’ (whatever ‘it’ happens to be that day), more unpredictability, and closer-knit/more casual culture. “Highway” people usually can’t handle the jungle, or even the dirt road.

Problems arise when a company has raised a seed or Series A and suddenly wants to present themselves as one of the big dogs by hiring someone with a very impressive resume and title. That person will very often want a compensation package that strains the company’s budget, and a level of resources and order that simply isn’t appropriate for early stage. Talent can come in the form of a lot of different cultures and personalities. Make sure you’re hiring talent with realistic expectations for your company’s stage. Salary v. equity expectations are often a valuable signal here, and can select for the right or wrong people.

And a big thing to watch out for: I’ve known of VCs who subtly push founder CEOs to hire “big company” people sooner than they are really needed, to create a greater sense of urgency in needing to raise a new round, that they lead. If an investor has put some seed or Series A money in your company and wants to lead your Series A or B, they have an incentive to shrink your runway by filling your payroll with high-salary people earlier than is appropriate.  More payroll means you’re forced to close your Series A (or Series B) sooner, and at a lower valuation, than you otherwise would’ve wanted; increasing their ownership. Be mindful of this dynamic, and ensure you have a total grasp of what your talent needs are and aren’t. 

Hiring Too Fast

You see far more companies that die because they hired too fast, and eventually couldn’t keep up with payroll, than the converse. Successful entrepreneurs know how to be scrappy and resourceful; seemingly magically figuring out a way to achieve results with far fewer resources than other people could. That should apply to hiring as well, and it’s often achieved by ensuring that you aren’t hiring “big company” people (see above) with (i) unrealistic salary expectations, and (ii) such specialized skillsets that they leave needs unfilled that require hiring more people.

Hiring extremely talented, flexible generalists appropriately suited (and compensated) for early-stage is often how resourceful CEOs keep their early-stage company “default alive” instead of “default dead,” to use Paul Graham’s language.  As a general matter, at early stage someone who is really good at X, Y, and Z is more valuable, and a much safer hire, than someone who is world class at just X.

Hiring Friends or Family

If you build anything that starts getting traction, there will come a time when people start suggesting their friends and family to fill job positions. In some sense, this is not a bad thing. Recruiting from your existing roster’s network is actually a very smart and common way to find quality candidates without needing to pay recruiters. The danger, of course, lies in the psychological tendency for immature founders to hire people simply because they like them, rather than because those people actually have the talent and skills the company needs. 

Only go down this path if you are 100% comfortable saying ‘no’ over and over again, because you’ll need to. Frankly, if you’re CEO and don’t know how to say “no” when you need to (often), you’re going to face much bigger problems than hiring. 

Friends and family are easy to hire, but they’re much harder to fire because of the emotional and political dynamics surrounding the personal relationship. And hiring people because of existing relationships, instead of because of merit, is also a fast way to create an insular, mediocre mono-culture of people who are all buddies with each other, as opposed to a performance driven one. As a resource-strapped early-stage company trying to navigate chaos, you can’t afford to have a low performance culture. Hire for merit from Day 1.

As I said, there are dozens of big mistakes companies make in hiring, and I’m sure there are fantastic blog posts out there from experts on the subject. The above is just a few really core tactical blunders VC lawyers see founder teams make, because we’re usually called in to help the team clean up the mess from a legal perspective.

In the early days, hire extremely talented, flexible and mature team-players with realistic expectations about startup life, not too early, and not just because you like them or they are someone’s friend. It’ll save you an enormous amount of headaches… and legal fees.

Early Hires: Options or Stock?

Nutshell:  While the conventional equity path of a startup is to issue (i) common stock to founders and (ii) options to employees, early hires concerned about taxes will often insist on receiving stock as well. Voting power, along with other political factors, present a few tradeoffs for founders to consider in that scenario.


  • Option Pool” – a portion of the company’s capitalization set aside (after founder stock is issued) for equity issuances to employees, consultants, advisors, etc., and subject to a special “plan” designed to comply with complex tax rules.  Even though it’s referred to as an “option” pool, properly designed equity plans will allow for direct stock issuances under the pool as well; not just options.
  • ISO – Incentive Stock Option – a tax-favored type of option issuable only to employees, if certain requirements are met. The main benefit is that upon exercise, the difference between the exercise price and the fair market value on the stock at the time of exercise is not taxed as ordinary income. However, it is subject to the Alternative Minimum Tax (AMT), which can hit certain people depending on their tax situation.
  • Restricted Stock” – For purposes of a private startup, just another way of saying Common Stock. The same security that founders get, except for non-founder employees it’s usually issued from the “pool” (under the Plan) using different form documents.
  • Early Exercise Options” – Conventional options issued to employees are not exercisable until they vest; meaning until the recipient has worked long enough to “earn” the right to exercise them.  Early exercise options have modified vesting/exercise provisions so that they can be exercised from Day 1 – with the underlying shares becoming subject to the vesting schedule.  From the Company’s perspective, early exercise options are very similar to restricted stock issuances. The only real difference is that the recipient has the option to exercise and receive the Stock on Day 1, or sit on it and exercise later.


The conventional path of a Company’s equity issuances goes something like this:

  • Founders receive direct issuances of Common Stock (not options)
  • Non-Founder employees receive ISOs (options)
  • Consultants, advisors, etc. receive NSOs (options)
  • Investors receive Preferred Stock, or SAFEs/Convertible Notes that convert into Preferred Stock


  •  The value of restricted stock is taxable as ordinary income on the date of issuance, unless its fair market value (FMV) is paid in cash.
  • Options, both ISOs and NSOs, however, are generally not taxable on the date of grant, as long as their exercise price is equal to the FMV.
  • So, you would normally expect employees to prefer receiving options over stock. No tax > Tax. And this is the case when the stock’s FMV is relatively high. That’s why later hires (usually after a Series A) almost always receive options, without question.
  • Stock gets to vote on stockholder approvals. Options do not (until they’re exercised for stock).

The Issues: Early employees want to minimize tax. Companies want to avoid giving away voting rights/complicating stockholder votes too early.

  • However, in the very early days of a startup’s life, avoiding tax on restricted stock is easy because of how low the FMV of the stock is (fractions of a penny): write a check for a few dollars (the full FMV), or just pay the tax on the few dollars of ordinary income.  You therefore get the “no tax on grant” benefit of options, without worrying about paying tax later on an exercise date.  Receiving stock also gets the clock running on long-term capital gains treatment.
  • Therefore, very early hires, when they do their homework, tend to insist on receiving restricted stock (or early exercise options) over conventional options. Better to deal with tax when the stock is worth (at least to the IRS) virtually nothing, instead of years later upon exercising the option when the tax bill could be much greater (ordinary income for NSOs, or AMT (for some people) for ISOs).
    • Sidenote: Conventional equity plans also have a 90-day post-termination exercise period, meaning, when an employees leaves a company (voluntarily or involuntarily) they have to exercise their options within 90 days, or they then get terminated – even if vested. Paying the exercise price isn’t an issue for an early hire in that scenario, because it’s very low (the fractions of a penny FMV), but if the AMT comes into play it can hit them with a tax bill.  This doesn’t come up in a Restricted Stock scenario.
  • The tradeoff from the Company’s perspective is that, just like founders, those hires that receive restricted stock will have full voting rights (including seeing whatever is submitted for stockholder votes) for all of their stock on Day 1, before they’ve vested in anything.  When only one or two people are in question, this may not be a big deal. It can be a way of making early employees feel like a part of the core team, because their equity is being treated just like founders.  When there are more than a handful of hires, however, it can get unwieldy fast. The number of people to consult for stockholder votes can go from 2-3 to 10, 15, 20. If there are consultants and advisors in the picture, they may start to ask why they aren’t getting the same tax benefits as early hires. And then at some point you have to draw a line and start granting options. Is the first optionee not as special as the restricted stock people? Politics. 

Generally speaking, the decision to give restricted stock v. options to very early hires is a practical/political one.  While the tax-favored nature of ISOs means that most early employees won’t see much of a tax difference between receiving ISOs v. restricted stock, the prospect of an AMT hit in the ISO scenario does make restricted stock, on net, better for recipients.  That needs to be balanced, on the company’s side, against the early voting power/information rights given away when an employee receives stock instead of options, and how it will play out with all of the company’s other hires.  

My general advice to founders is to be aware of the tradeoffs, and to consciously treat the early voting power and tax benefits associated with restricted stock as currency not to be wasted.  If there’s a very early superstar that you deliberately want to single out as a key player, use the currency.  If not, then make the decision based on all the other factors. Company culture will likely factor greatly into the calculus.  Many, many founders prefer to avoid the politics/complications and simply draw a line at the founder (stock)/non-founder (option) division.  Others are more selective. There’s no magic formula.

A few separate issues worth addressing:

  • The 90-day post-termination exercise period (after which unexercised options, vested or not, are terminated) often gets criticized as being unfair to employees, and there’s some justification for that criticism. The view is that the employee shouldn’t be forced to “use it or lose it” if they did their time (their option vested) and are now moving on to a new company.
    • The actual 90-day number comes from tax rules requiring that ISOs be exercisable only within 90 days of termination.  If an option is exercisable after that, it automatically becomes an NSO for tax purposes. But there’s nothing in the tax rules requiring that the option be terminated at 90 days. That’s largely meant (i) as a deterrent (frankly) to people quitting, and (ii) a way to clean up the cap table for people who didn’t want to pay their exercise price, allowing that portion of the pool to then be re-used for new hires.
    • While the 90-day period is still convention, key executives/hires will often either negotiate for an extended exercise period for their own grants, or the Company will as a gesture of good will, decide on its own to selectively extend the period when someone leaves on good terms.

Obligatory Disclaimer: This post contains a lot of fundamentals and generalizations on tax rules, but it’s obviously not intended to be an exhaustive statement of those rules. Circumstances vary, and you should absolutely not rely on this post without consulting your own attorney and/or tax advisors.  If you do, don’t blame me when it blows up in your face.  You’ve been warned.